This compound belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.
External Descriptors
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1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
Not applicable. No immunoassay or bioanalytical “kit-like” protocols are associated with this small-molecule reagent. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for generalized procedures and adapt to your lab’s SOPs.
Biological Roles
Item-specific biological data are not provided and this product is for research use only.
General context (literature):
Aromatic nitriles are not typical endogenous metabolites in mammals. However, nitrile functions occur in some natural products and agrochemicals.
Biotransformations: Nitrilases and nitrile hydratases (from bacteria/fungi) can hydrolyze aryl nitriles to the corresponding amides/acids under mild conditions; biocatalysis can be leveraged in green synthesis.
ADME-relevant features (conceptual): The para-nitrile imparts electron-withdrawing character and can modulate lipophilicity and metabolic stability in medicinal chemistry scaffolds. The ethyl substituent increases hydrophobicity and can be a site for oxidative metabolism (benzylic oxidation) in microsomes.
No clinical or therapeutic claims are made. For any biological screening, ensure appropriate controls and safety assessments.
Buffer Applications
Not typically applicable. 4-Ethylbenzonitrile is a neutral, hydrophobic organic building block and is not used as a buffering agent. For experimental work involving this compound, select buffers only to support an aqueous phase in biphasic reactions or extractions; the compound itself does not impart buffering capacity.
Green Alternatives
While 4-ethylbenzonitrile itself is a target/intermediate rather than a solvent, greener choices can be made for the processes using it.
Greener solvent choices for common operations (literature guidance):
Replace chlorinated solvents (DCM, DCE) with ethyl acetate, 2-MeTHF, CPME, or greener alcohols where feasible.
For organometallic additions to the nitrile, 2-MeTHF or CPME can substitute for THF/diethyl ether, offering higher boiling points and better sustainability.
In hydrogenations, use ethanol or isopropanol as solvent and optimize for low catalyst loadings and H2 pressure.
For hydrolysis, aqueous media with minimal organic cosolvent can reduce solvent volume and hazards.
Trade-offs to consider:
2-MeTHF/CPME may change selectivity in lithiation or hydride reductions and can retain water; rigorous drying may be needed.
Ethyl acetate may not dissolve highly polar reagents; MeCN can be a good compromise but has its own environmental profile.
Small comparison (general):
THF vs 2-MeTHF: similar polarity; 2-MeTHF is bio-based and forms peroxides more slowly, with higher bp aiding heat management.
DCM vs EtOAc: EtOAc is less toxic and biodegradable, though less ideal for very nonpolar analytes and may coelute in GC.
Process intensification:
Flow chemistry for nitrile reductions or benzylic halogenations can improve safety and minimize solvent and waste.
Pharmaceutical Uses
No pharmacopeial or excipient status is specified for this item; refer to CoA/Spec Sheet if needed.
General formulation/manufacturing context (literature):
Role: Used as a synthetic intermediate in medicinal chemistry and process chemistry to access para-substituted benzoic acids, benzylamines, aryl ketones, and related scaffolds.
Advantages: The nitrile can serve as a bioisostere of carbonyls in discovery programs and as a masked carboxamide/acid group that can be unveiled late-stage via hydration/hydrolysis.
Considerations: Residual aromatic nitriles in drug substance/drug product are typically controlled impurities; analytical methods (GC, GC–MS, HPLC) must be developed for purge verification.
No therapeutic or clinical claims are made. Research use only.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general physical data for 4-ethylbenzonitrile (for planning purposes only; not product specifications):
State at RT: typically a colorless to pale liquid or low-melting solid depending on purity and temperature.
Boiling point: ~232–238 °C (literature, at 1 atm).
Melting point: often below room temperature; reported to be near or below 0 °C (literature, varies with purity).
Density: ~0.98–1.01 g/mL at 25 °C (literature).
Refractive index: n20 D ~1.510–1.515 (literature).
Aqueous solubility: very low; soluble/miscible with common organic solvents (EtOAc, DCM, toluene, THF, MeCN, alcohols) (literature).
UV-Vis: aromatic π–π* absorption in the 200–270 nm region (literature); nitrile shows a weak n→π* feature in the deep UV.
Notes for practical work (general):
The nitrile group is strongly polarizable but nonprotic; dielectric behavior resembles other aryl nitriles.
Ensure measurements (e.g., refractive index, density) are taken at defined temperatures and with calibrated instruments for method development.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on quality considerations for 4-ethylbenzonitrile (general):
Typical impurities in aryl nitriles may include unreacted precursors (e.g., haloarenes, amides), isomeric alkylbenzonitriles, benzylic oxidation products, residual solvents, and trace metals from synthesis catalysts.
If using for analytical or kinetic studies, consider GC, GC–MS, or 1H/13C NMR to verify isomeric purity (para vs meta/ortho) and benzylic integrity.
Water, peroxide, and UV-cutoff specifications: Not specified for this item; refer to CoA/Spec Sheet.
If low UV background is needed (e.g., HPLC detection at 210–254 nm), ensure an appropriate chromatography grade or pre-verify baseline.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Aryl nitriles are typically supplied neat without stabilizers.
CoA/SDS linkage to use:
For regulated or GMP-adjacent workflows, request batch-specific CoA detailing assay (%), GC purity, and residual solvent/metals. Align acceptance criteria with internal specifications.
Reaction and Applications
As a para-alkyl-substituted aryl nitrile, 4-ethylbenzonitrile is a versatile intermediate. The nitrile group and benzylic ethyl side chain enable orthogonal transformations.
Representative application families (literature):
Nitrile transformations:
Hydrolysis to amide (Beckmann-adjacent pathways not needed) or to carboxylic acid under acidic (H2SO4, HCl, Δ) or basic (NaOH, Δ) conditions.
Reductions: to primary amine (catalytic hydrogenation, Raney Ni/Pd/C; or LiAlH4), to aldehyde (DIBAL-H, −78 °C, then quench), or to imine/enamine under controlled conditions.
Nucleophilic addition: Grignard or organolithium addition to the nitrile carbon to afford the corresponding ketone after hydrolysis (use 1 equiv RMgX/RLi; then acidic workup).
Benzylic functionalization of the ethyl group:
Radical bromination (NBS, AIBN, hv) to access p-cyanobenzyl bromides for subsequent substitutions or cross-couplings.
Oxidation to p-cyanopropiophenone or p-cyanophenylacetic derivatives (e.g., SeO2 allylic/benzylic oxidation; MnO2 for benzylic alcohols if pre-formed).
Directed ortho-metalation (DoM): the nitrile acts as a directing group; with strong bases (s-BuLi/TMEDA) at −78 to −40 °C, ortho-lithiation adjacent to CN can be achieved, enabling electrophile introduction (D, 13C, halogens, formyl, etc.).
Cross-coupling sequences: After installing a leaving group benzylically or ortho to CN, Pd/Ni-catalyzed couplings (Suzuki–Miyaura, Buchwald–Hartwig after amination) expand substitution patterns.
Use contexts:
Employed as a hydrophobic, electron-withdrawing arene in medicinal chemistry SAR.
Intermediate en route to para-ethylbenzoic acid, benzylamines, aryl ketones, and heteroaryl elaborations via ketone/nitrile chemistry.
Reaction Conditions
General literature conditions for common transformations of 4-ethylbenzonitrile (guidance only; optimize per lab):
Hydrolysis to amide/acid:
Acidic: conc. H2SO4 or 6 M HCl, 80–120 °C, 4–24 h → amide/acid depending on water content; neutralization and extraction workup.
Basic: KOH/NaOH (2–6 M) in EtOH/H2O or dioxane/H2O, reflux 6–24 h → carboxylate; acidify to isolate acid.
Reduction of nitrile:
To primary amine: H2 (3–10 bar) over Pd/C or Raney Ni in EtOH/MeOH, 25–60 °C, 4–16 h; or LiAlH4 in THF/Et2O, 0–25 °C, 1–4 h (cautious quench).
To aldehyde: DIBAL-H (1.1–1.5 equiv) in toluene/hexanes at −78 °C, 1–2 h; careful aqueous quench at low temperature, then warm-up and extract.
Addition of organometallics (to form ketones): RMgX (1.1–1.5 equiv) or RLi (1.0–1.2 equiv) in THF/Et2O at −78→0 °C, 1–3 h; acidic hydrolysis to unveil the ketone. Avoid over-addition by controlling stoichiometry and temperature.
Benzylic bromination:
NBS (1.1–1.2 equiv), AIBN (cat.), CCl4 or greener alternatives like PhMe or tBuPh/MeCN mixtures; reflux or hv; 2–8 h. Monitor by GC/1H NMR.
Directed ortho-metalation (DoM):
s-BuLi (1.1–1.5 equiv) with TMEDA in hexanes/THF at −78 °C, 0.5–2 h; quench with electrophile (D2O, I2, DMF, B(OMe)3). Strict anhydrous conditions required.
Typical yields: highly method- and substrate-dependent; 50–90% is common for well-optimized steps. Always run small-scale scouts to establish chemoselectivity with the ethyl side chain present.
Safety and Handling
Item-specific hazard data: Not specified in Product Data. Always consult the product SDS for authoritative information before use.
General GHS guidance for aryl nitriles (literature-based; not item-specific):
Potential hazards: Combustible liquid; may cause skin/eye irritation; harmful if swallowed or inhaled; may cause respiratory irritation on high vapor/aerosol exposure.
Pictograms and H-statements: Not specified for this item; refer to SDS.
Best-practice PPE and handling (general):
Use in a fume hood; avoid inhalation of vapors/mists.
Wear appropriate PPE: lab coat, safety glasses or goggles, and chemical-resistant gloves (e.g., nitrile gloves). Consider a face shield for scale-up.
Avoid contact with strong oxidizers, strong bases/acids under forcing conditions (which can promote hydrolysis or side reactions), and strong reducing agents unless intended.
Spill control: Absorb with inert material (vermiculite, diatomaceous earth); collect in suitable container for disposal. Prevent entry to drains.
First aid (overview): Move exposed persons to fresh air; rinse skin/eyes with water for ≥15 min; seek medical attention if symptoms persist; if ingested, do not induce vomiting—seek immediate medical advice. Defer to SDS.
Storage and stability:
Storage Conditions per Product Data: Room temperature; keep tightly closed in a dry, well-ventilated area.
Protect from heat/sparks/open flame. Store away from oxidizers.
No known tendency for peroxide formation (non-ether).
Solvent Selection
This product is an aromatic building block, not a solvent. Solvent selection therefore focuses on dissolving it efficiently and enabling transformations.
General solvent compatibility (literature):
High solubility in moderately polar aprotic solvents: THF, DCM, DCE, EtOAc, MeCN, DMF, DMSO.
Good solubility in nonpolar aromatics: toluene, xylenes.
Limited solubility in water; biphasic methods may require phase-transfer or co-solvents.
Choosing a solvent by application:
Metalations/benzylic functionalization: anhydrous ethers (THF, MTBE) or hydrocarbons (toluene, heptane) at low temperature for controlled lithiation or radical bromination (NBS/AIBN).
Nitrile reductions (to amines/alcohols): ethanol, IPA, or THF with hydrogenation catalysts or hydrides (BH3·THF, LiAlH4). For partial reductions, use DIBAL-H in toluene/hexanes at ≤ −78 °C.
Hydrolysis to amide/acid: aqueous alcohols or dioxane/water with mineral acids or bases; consider MeCN or DMF as co-solvents if solubility is limiting.
Cross-couplings after benzylic halogenation/oxidation: polar aprotics (DMF, DMAc, NMP) or mixed systems with toluene/THF when using Pd/Ni catalysts.
Analytical considerations:
Sample prep for GC/GC–MS: hexanes or DCM; avoid strongly protic solvents that could complicate baseline at low UV wavelengths.
For HPLC-UV, MeCN/water or MeOH/water gradients detect strongly at 210–230 nm; aromatic absorbance allows 254 nm monitoring.
Storage and Reconstitution
Storage (item-specific): Room temperature (per Product Data). Keep container tightly closed in a dry, well-ventilated place.
Shipping: Normal (per Product Data).
Reconstitution: Supplied neat; no reconstitution required. If received as a solid (temperature dependent), gently warm to ambient and ensure homogeneity before use.
Handling notes:
If long-term storage is anticipated, consider storing under inert gas to minimize slow oxidative discoloration, and protect from strong light/heat.
Avoid moisture ingress; while nitriles are hydrolytically robust at neutral pH, prolonged exposure to strong acids/bases can lead to hydrolysis.
Stability: Aryl nitriles are generally stable at ambient conditions. Always consult the CoA/SDS for any batch-specific guidance.
Research Use Note: For research use only.
Structure and Identity
Brief description: 4-Ethylbenzonitrile is a para-ethyl–substituted aryl nitrile (benzonitrile core with an ethyl group at the 4-position), commonly used as a hydrophobic aromatic building block in synthesis.
Item-specific (from Product Data)
SKU: E169049
Product Name: 4-Ethylbenzonitrile
CAS: 25309-65-3
CID: 91393
InChIKey: 347726 (as provided)
Storage Conditions: Room temperature
Shipped In: Normal
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general identifiers (for reference; not item specifications)
Functional groups: aromatic ring; nitrile (–C≡N) at para position; ethyl substituent para to nitrile.
2D description: A benzene ring bearing a nitrile at C1 and an ethyl at C4 (para relationship), giving a linear, conjugation-withdrawing CN group opposing a mildly donating alkyl.
Stereochemistry: None (achiral).
Synthetic Utility
Key reactivity handles:
Nitrile carbon (electrophilic):
Addition of organometallics (RMgX/RLi) to form imines that hydrolyze to ketones (ketone synthesis strategy from nitriles).
Reductions to amines (LAH, catalytic hydrogenation) or aldehydes (DIBAL-H, careful temperature control), enabling divergent routes.
Hydrolysis to primary amide or carboxylic acid, allowing late-stage polarity increase or coupling.
Aromatic ring (activated/deactivated pattern):
Nitrile is meta-directing in electrophilic aromatic substitution; ethyl is ortho/para-directing—net reactivity is reduced by CN but benzylic positions remain susceptible to free-radical halogenation.
Directed ortho-metalation adjacent to CN with strong bases provides access to ortho-functionalized derivatives that are otherwise challenging.
Benzylic ethyl group:
Bromination (NBS), oxidation (e.g., via Cr(VI)-free methods: TEMPO/bleach after alcohol formation, or IBX), and conversion to Grignard/organozinc reagents after halogenation for cross-couplings.
Retrosynthetic value:
Serves as a convergent node: ring installed via nitrile-bearing building block; side chain diversified late by benzylic chemistry; nitrile converted to acid/amine as required.
Useful in iterative SAR where CN tunes electronics and H-bond acceptor capacity without adding HBD functionality.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and is not an antibody, enzyme, or affinity reagent. No target or epitope specificity applies.
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